Olivia Wilde

The Agent- Olivia Wilde

You had held a barbeque at the house the following weekend that Sunday for Danica with all her friends and family along with some of your talent, including Cobie Smoulders, who was now one of the higher up talents you had given to Danica to manage. But to seal the deal with Cobie, well, you had to give her what she wanted. And all the looks, jokes at your expense and needing Danica to come "save the day" and other little flirtations led to her holding the sink in the master bathroom, her summer dress hiked up over her thighs as she held her ass back as you were plunging in and out of her ass, Cobie biting her dress to stifle her screams as six inches rocked in and out of her asshole quickly as you grabbed and smacked her ass cheeks before you pulled out and slapped her ass cheeks with your hard cock before re-entering her, Cobie sucking her teeth as she groans and then mutters something as you pulled at her hair and slammed your hips harder and deeper as Cobie shuddered and came as her other hand rubbed her pussy and got an orgasm out of her body as she drove her hips back and added more of your dick into her rectum before you pulled out and pushed into her pussy, causing her to scream out as she then giggled and threw her hips back happily to match you quick pace as your balls swung and churned as she just closed her eyes and pushed back against you for a few minutes before she cried out and orgasmed hard, drenching your dick with orgasmic fluids before you grunted out and thrusted hard a few times, slamming deep as her entire body rocked to every thrust as her ass cheeks smacked against your waist loudly before you buried in deep and started to cum, filling her pussy with thick ropes of jizz as Cobie just moaned loudly, panting and groaning as she twisted her hips back and forth as she coated her inner walls with your cum as you took deep breaths and smirked as she pulled herself off and pushed two fingers inside to keep the cum from pouring out.

You both composed yourself and went to the kitchen, Cobie sitting on the counter as you made drinks as everyone was still outside and around the pool as she said she always liked Danica and wondered how you know she'll be a good agent. You explained the thought process and Cobie nodded and seemed to agree as she said she would send word around. She asked how you were acclimating to the house being yours and you said it was both fitting and odd sometimes, as you said you could sometimes see old memories when you were alone. Cobie told you about some scientific phenomenon that was called and the two of you just chit chatted until someone came in and told you to come back to eat with everyone, Cobie winking at you as you joined the fray with everyone else.

You, Danica, Eliza, Alex Morgan and some other friends had stayed well into the night as Danica thanked you for the evening and you tapped beers and took a drink as she asked if you were prepped for your meeting tomorrow, which you assured her you were. There was a bidding war for Olivia Wilde's next film, and while you weren't part of the producers bidding war, you were going in to try and secure the casting and you needed Olivia on board to package your agency as part of the deal. Olivia had been a talent as an actor for CAA but was now freelance as a director following the success of Booksmart, and the only reason you were getting the meeting was because of her admiration and closeness with Kaitlyn. Danica was flying out to deal with Elizabeth Olson who was still pushing back against Disney and the enforcement of her contract, though you had smoothed things over with Scarlett who was coming to see the house soon. You prepped Danica on dealing with Elizabeth, while Danica was also setting you up with a number of sports free agents in the upcoming summer months while you were still also having to keep the sports entertainment recruitment up as well. Danica had already gotten a few commitments, including stealing actor Sebastian Stan away from his deal, another MCU coup. She was only an agent for a few weeks and had paid good dividends. You said as much and watched her blush as you eventually called it a night but told her they were welcome to stay as you had to get up relatively early to meet up with Olivia. You said goodnight to everyone and took a while to fall asleep but eventually did after throwing on your favorite movie.

You awoke as the sun was coming up, showering and dressing while calling Kaitlyn who had told you to do so so she could tell you things about Olivia she thought would help you understand her thought processes. You made coffee, grabbed a bagel and drove into the city, arriving early at the restaurant only to be surprised that Olivia was already there. You shook hands, cheek kissed and ordered breakfast while making small talk before Olivia very matter of factly asked what you were looking for and using the information you had from Kaitlyn gave your sphill and pitch as to why your agency should be involved with the casting for her next film. She didn't say much other then a few inquisitive questions but you handled the questions as well as you coole, sticking to your vision of cooperation with her and how you were trying to change things within the agency, which got a scoff from her but you pointed out the last few years and how you were. Olivia seemed to take that in mind but you could never really tell as she never gave anything away, through facial cues or even the words she spoke afterwards. As you finished the pitch and the breakfast you weren't nearly as confident as you had been and Olivia paid and was cordial while saying she would think things over. You knew that didn't mean much, but didn't betray that as you thanked her for the time. She asked about Kaitlyn and you tried to be diplomatic but she said she knew you two were some form of a item and so you felt a bit more relaxed and just talked to her as you normally would with someone in the know, getting more words out of her in her admiration for Kaitlyn then from the conversation about her film. When she said she had to get going you wished her the best for her film and got her to smile as she headed out as you decided to go to the office and tell Danica about what happened.

Danica wasn't in yet by the time you got to the office and you called Kaitlyn and got her voicemail, and feeling a bit deflated you laid on the fold out couch in the office and took a nap, waking up eventually to Danica standing over you with a look of someone who had drank a little too much. You followed her to her office now and saw Eliza at the reception desk looking also a bit out of it as you chuckled as Danica sat behind her desk and told you to tell her everything. You gave the entire conversation and Danica listened intently, nodding and making little noises as she said it was fifty fifty. You didn't know whether that was good or bad and she admitted she would've dropped the ball so you did what you could. You talked for an hour about what to do next and you made your flights for the next few days of business while Danica headed off to catch her flight out to Georgia. You have Eliza the rest of the day off so she could get a Danica to the airport and she thanked you as you headed back out to the house to work from home as you didn't want to stay in the office and have to beat the traffic home later on.

You worked in the office for the rest of the day, only looking up from your laptop and phone when your doorbell went off. Not expecting anyone you checked the ring camera and saw who it was, your curiosity peaked as you went and opened up to see Olivia Wilde standing at your doorway, smirking as she walked past you and into your home as she looked around and asked if Kaitlyn was wrong about you. She gave you the look and you chuckled and said it depends on what Kaitlyn had said and she came and grabbed your crotch, telling you she's been without a man since her ex Harry Styles cheated on her, Kaitlyn had said someone like you could give her the release she craves and she tells you to take your pants off as you did as you were told, watching her face as she studied you carefully, eying your cock as she grinned and said it would definitely do. She asked where the bedroom was and you told her as you followed behind as she stripped her clothes off on the walk up the stairs and down the hall until she reached the room. She turned and face you, pressing her nude body against you as she said she was gonna take the deal out of a favor for Kaitlyn as you represented her and she wanted to cast her for the next movie she was working on. She kissed you passionately while climbing into your arms as you held her up and wrapped her legs around your waist as you made out with the actress turned director, letting her grins herself up and along your growing bulge as you walked her to the bed and lined yourself up, pushing your hips forward as she gripped your face and quivered as she felt you sliding inside of her with no hesitation as her pussy was already dripping wet.

Olivia kept her arms around your neck, rubbing your hair and scratching along your shoulders depending on the pace as you grinding seven inches repeatedly, every now and again picking up speed and deliver hard quick thrusts, making her body slap under you as you drove your hips inside as she ran her smooth legs along the back of your own as she would kiss you and then break the kiss to throw her head back and scream out as she would orgasm and extra wetness made the squelching noise grow loud as her mound was a wet mess, and your thick manhood repeatedly sliding and crashing inside only added to it as She grabbed the back of your head and placed it against her chest as you licked and kissed at it while still laying in hard sharp thrust.

Olivia was on top now, grabbing the headboard as you sucked at her breasts, licking and biting while your hands held onto her hips and your feet pushed against the bed as she rocked her hips down, pounding herself as your mound was covered in wetness as she was leaning between your crotches as she just continued to fuck herself wildly, pushing through her spasming orgasms as she would rock down, and the extra attention to her nipples was only quickening the amount of her orgasms and as she continues to constrict up tighter and tighter with every passing orgasm, she slammed herself down and held her hips over your throbbing manhood as she grinded back and forth, stirring your dick against her spasming inner walls as she felt your throbbing pushing against her clenched up womanhood and she cries out as you started to thrust up and out of her relentlessly, pounding her cunt for a few minutes until you erupted, grunting loudly as she came nearly at the same time as her wetness made her pussy a creamy mess, as thick ropes of cum was firing into her womb and drizzling down along her inner walls, staining her insides as she coos happily and kisses you as she grinded herself slowly, stirring your rod around her cunt as she shudders and came a final time as your jerking and pulsating slowly softened while still being deep inside of her.

Olivia laid in bed, propped up on her elbow as she asked who all you were bedding in a regular and you said you didn't want to say too much out of respect for them. She laughed and said as long as you take care of Kaitlyn and don't play with her heart she would be a loyal friend. You asked about how her relationships ended up the way they did and she seemed to be put off by it and so you talked about what had happened to Caity and the hardships of your old monogamous relationships and how they never worked out either. You talked for a good hour before the cuddling eventually caused Olivia to fall asleep and you thought about everything and smiled as you looked at the sleeping starlet and then closed your eyes before trailing off into a happy slumber.

End of chapter.